Organic light-emitting device

ABSTRACT

Embodiments of the present invention are directed to a heterocyclic compound and an organic light-emitting device including the heterocyclic compound. The organic light-emitting devices using the heterocyclic compounds have high-efficiency, low driving voltages, high brightness and long lifespans.

CROSS-REFERENCE TO RELATED PATENT APPLICATION

This application claims priority to and the benefit of Korean PatentApplication No. 10-2009-0082566 filed on Sep. 2, 2009 in the KoreanIntellectual Property Office, the entire content of which isincorporated herein by reference.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The present invention relates to heterocyclic compounds and organiclight-emitting devices including the heterocyclic compounds.

2. Description of the Related Art

Organic light-emitting devices are self-emission type display devices,and have wide viewing angles, high contrast ratios, and short responsetimes. Due to these characteristics, organic light-emitting devices aredrawing much attention.

Light-emitting devices can be roughly classified into inorganiclight-emitting devices which include emission layers containinginorganic compounds, and organic light-emitting devices which includecontaining organic compounds. Organic light-emitting devices have higherluminance, lower driving voltages, and shorter response times thaninorganic light-emitting devices. In addition, organic light-emittingdevices produce various colors. Thus, research has been conducted intoorganic light-emitting devices.

Typically, an organic light-emitting device has a stack structureincluding an anode, a cathode and an organic emission layertherebetween. However, a hole injection layer and/or a hole transportlayer may be further stacked between the anode and the organic emissionlayer, and/or an electron transport layer may be further stacked betweenthe organic emission layer and the cathode. In other words, an organiclight-emitting device may have an anode/hole transport layer/organicemission layer/cathode stack structure, or an anode/hole transportlayer/organic emission layer/electron transport layer/cathode stackstructure.

As a material for forming the organic emission layer, an anthracenederivative may be used. However, organic light-emitting devicesincluding known light-emitting materials do not have satisfactory lifespan, efficiency, or power consumption characteristics, thus leavingmuch room for improvement.

SUMMARY OF THE INVENTION

According to embodiments of the present invention, a heterocycliccompound has improved electrical characteristics, charge transportingcapabilities and light-emission capabilities.

In some embodiments of the present invention, an organic light-emittingdevice includes the heterocyclic compound.

In other embodiments of the present invention, a flat panel displaydevice includes the organic light-emitting device.

According to some embodiments of the present invention, an organiclight-emitting device includes at least one layer containing theheterocyclic compound, where the at least one layer is formed using awet process.

According to embodiments of the present invention, a heterocycliccompound includes compounds represented by Formula 1 below:

In Formula 1, each of R₁ through R₁₁ is independently selected fromhydrogen atoms, heavy hydrogen atoms, substituted and unsubstitutedC₁₀-C₅₀ alkyl groups, substituted and unsubstituted C₃-C₅₀ cycloalkylgroups, substituted and unsubstituted C₁-C₅₀ alkoxy groups, substitutedand unsubstituted C₅-C₅₀ aryloxy groups, substituted and unsubstitutedC₅-C₅₀ arylthio groups, substituted and unsubstituted C₅-C₆₀ arylgroups, amino groups substituted with at least one R₅-R₅₀ aryl group,substituted and unsubstituted C₄-C₆₀ heteroaryl groups, substituted andunsubstituted C₆-C₆₀ condensed polycyclic groups, halogen atoms, cyanogroups, nitro groups, hydroxyl groups, and carboxyl groups. Neighboringsubstituents selected from R₁ through R₁₁ may optionally bond to eachother, thereby forming an aromatic ring.

R₁ may be selected from unsubstituted and substituted monocyclic totricyclic aryl groups. The unsubstituted monocyclic to tricyclic arylgroups may be selected from phenyl groups, naphthyl groups, biphenylgroups, terphenyl groups, anthracenyl groups, fluorenyl groups, andcarbazolyl groups. The substituted monocyclic to tricyclic aryl groupsmay be selected from phenyl groups, naphthyl groups, biphenyl groups,terphenyl groups, anthracenyl groups, fluorenyl groups, and carbazolylgroups substituted with at least one substituent selected from C₁-C₅alkyl groups, C₁-C₅ alkoxy groups, cyano groups, amine groups, phenoxygroups, phenyl groups and halogen groups.

R₇ may be selected from unsubstituted and substituted monocyclic totricyclic aryl groups, and unsubstituted and substituted C₁₂-C₅₀arylamine groups. The unsubstituted monocyclic to tricyclic aryl groupsmay be selected from phenyl groups, naphthyl groups, biphenyl groups,terphenyl groups, anthracenyl groups, fluorenyl groups and carbazolylgroups. The substituted monocyclic to tricyclic aryl groups may beselected from phenyl groups, naphthyl groups, biphenyl groups, terphenylgroups, anthracenyl groups, fluorenyl groups, and carbazolyl groupssubstituted with at least one substituent selected from C₁-C₅ alkylgroups, C₁-C₅ alkoxy groups, cyano groups, amine groups, phenoxy groups,phenyl groups, and halogen groups. The substituted C₁₂-C₅₀ arylaminegroups may be selected from groups substituted with a substituentselected from C₁-C₅ alkyl groups, C₁-C₄ alkoxy groups, cyano groups,amine groups, phenoxy groups, phenyl groups, and halogen groups.

Each of R₂ and R₃ may independently be selected from methyl groups andphenyl groups.

Each of R₅ and R₁₀ may independently be selected from t-butyl groups,phenyl groups, naphthyl groups, and fluorenyl groups.

In some embodiments, the heterocyclic compound may include one ofCompounds 11, 29, 43, 56, 74 and 82 below:

According to other embodiments of the present invention, an organiclight-emitting device including a first electrode, a second electrode,and at least one organic layer between the first electrode and thesecond electrode. The at least one organic layer includes at least onelayer including the heterocyclic compound.

The organic layer may include an electron injection layer or an electrontransport layer.

The organic layer may include a single layer having both electroninjection and electron transport capabilities.

The organic layer may include an emission layer.

The organic layer may include an emission layer, and the heterocyliccompound may be used as a fluorescent or phosphorescent host.

The organic layer may include an emission layer, and the heterocyliccompound may be used as a fluorescent dopant.

The organic layer may include an emission layer and an electroninjection layer or an electron transport layer, and the emission layermay include an anthracene compound.

The organic layer may include an emission layer and an electroninjection layer or an electron transport layer, and the emission layermay include an arylamine compound.

The organic layer may include an emission layer and an electroninjection layer or an electron transport layer, and the emission layermay include a styryl compound.

The organic layer may include an emission layer, and an electroninjection layer or an electron transport layer, and the emission layermay include a red emission layer, a green emission layer, a blueemission layer, or a white emission layer, each of which may include aphosphorescent compound.

The organic layer may include at least one layer selected from a holeinjection layer, a hole transport layer, an electron blocking layer, anemission layer, a hole blocking layer, an electron transport layer, andan electron injection layer.

The organic light-emitting device may have a first electrode/holeinjection layer/emission layer/second electrode structure, a firstelectrode/hole injection layer/hole transport layer/emissionlayer/electron transport layer/second electrode structure, or a firstelectrode/hole injection layer/hole transport layer/emissionlayer/electron transport layer/electron injection layer/second electrodelayer structure.

According to embodiments of the present invention, a flat panel displaydevice includes the organic light-emitting device described above, wherethe first electrode of the organic light-emitting device is electricallyconnected to a source electrode or a drain electrode of a thin-filmtransistor.

According to other embodiments of the present invention, an organiclight-emitting device includes a first electrode, a second electrode,and an organic layer between the first electrode and the secondelectrode. The organic layer includes at least one layer comprising theheterocyclic compound, which layer can be formed using a wet process.

BRIEF DESCRIPTION OF THE DRAWINGS

The above and other features and advantages of the present inventionwill become more apparent by reference to the following detaileddescription when considered in conjunction with the attached drawing inwhich:

FIG. 1 is a schematic diagram depicting the structure of an organiclight-emitting device according to an embodiment of the presentinvention.

DETAILED DESCRIPTION OF THE INVENTION

The present invention will now be described with reference to theaccompanying drawings, in which exemplary embodiments of the inventionare shown.

A heterocyclic compound according to an embodiment of the presentinvention is represented by Formula 1 below:

In Formula 1, each of R₁ through R₁₁ is independently selected fromhydrogen atoms, heavy hydrogen atoms, substituted and unsubstitutedC₁-C₅₀ alkyl groups, substituted and unsubstituted C₃-C₅₀ cycloalkylgroups, substituted and unsubstituted C₁-C₅₀ alkoxy groups, substitutedand unsubstituted C₅-C₅₀ aryloxy groups, substituted and unsubstitutedC₅-C₅₀ arylthio groups, substituted and unsubstituted C₅-C₆₀ arylgroups, amino groups substituted with at least one R₅-R₅₀ aryl group,substituted and unsubstituted C₄-C₆₀ heteroaryl groups, substituted andunsubstituted C₆-C₆₀ condensed polycyclic groups, halogen atoms, cyanogroups, nitro groups, hydroxyl groups, and carboxyl groups. Neighboringsubstituents selected from R₁ through R₁₁ may optionally bond to eachother, thereby forming an aromatic ring.

Anthracene derivatives have been as materials for an organic emissionlayer. For example, organic light-emitting devices have beenmanufactured using phenylanthracene dimers or trimers. However, suchorganic light-emitting devices have narrow energy gaps and lowerblue-light color purity since two or three oligomeric species ofanthracene are linked by conjugation. In addition, such compounds arehighly vulnerable to oxidation and thus are liable to produceimpurities, necessitating purification.

In an effort to address these drawbacks, organic light-emitting deviceshave been manufactured using anthracene compounds including naphthalenesubstituted for anthracene at the 1 and 9 positions, and devises havealso been manufactured using diphenylanthracene compounds including anaryl group substituted for a phenyl group at the meta position. However,these organic light-emitting devices have lower light-emissionefficiency.

In addition, organic light-emitting devices have been manufactured usinga naphthalene-substituted monoanthracene derivative. However, thelight-emission efficiency thereof is low (at about 1 cd/A), and thussuch organic light-emitting devices are not suitable for practical use.

Furthermore, organic light-emitting devices have been manufactured usinga phenylanthracene compound including an aryl substituent at the metaposition. Such a compound has sufficient thermal resistance but lowlight-emission efficiency of about 2 cd/A. Thus, further improvement isrequired.

The heterocyclic compounds of Formula 1 according to embodiments of thepresent invention may be suitable as a material for an emission layer(EML) and/or an electron transport layer (ETL) or an electron injectionlayer (EIL) of an organic light-emitting device. The heterocycliccompounds of Formula 1 have high glass transition temperatures (Tg) ormelting points due to the introduction of the heterocyclic group. Thus,the heterocylic compounds have thermal resistance against Joule heatgenerated in an organic layer, between organic layers, or between anorganic layer and a metallic electrode when light emission occurs, andare highly durable in high-temperature environments.

According to embodiments of the present invention, an organiclight-emitting device manufactured using a heterocyclic compound ofFormula 1 (which includes an anthracene group and an indole group fusedthereto) has good durability when stored or operated. In addition, dueto the introduction of a substituent such as a fluorene group, molecularfilms may be maintained in good condition, thereby improving thecharacteristics of the organic light-emitting device.

The substituents in the heterocyclic compound of Formula 1 will now bedescribed. In Formula 1, R₁ may be selected from unsubstituted andsubstituted monocyclic to tricyclic aryl groups. The unsubstitutedmonocyclic to tricyclic aryl groups may be selected from phenyl groups,naphthyl groups, biphenyl groups, terphenyl groups, anthracenyl groups,fluorenyl groups, and carbazolyl groups The substituted monocyclic totricyclic aryl groups may be selected from phenyl groups, naphthylgroups, biphenyl groups, terphenyl groups, anthracenyl groups, fluorenylgroups, and carbazolyl groups substituted with at least one substituentselected from C₁-C₅ alkyl groups, C₁-C₅ alkoxy groups, cyano groups,amine groups, phenoxy groups, phenyl groups and halogen groups.

R₇ may be selected from unsubstituted and substituted monocyclic totricyclic aryl groups, and unsubstituted and substituted C₁₂-C₅₀arylamine groups. The unsubstituted monocyclic to tricyclic aryl groupsmay be selected from phenyl groups, naphthyl groups, biphenyl groups,terphenyl groups, anthracenyl groups, fluorenyl groups and carbazolylgroups. The substituted monocyclic to tricyclic aryl groups may beselected from phenyl groups, naphthyl groups, biphenyl groups, terphenylgroups, anthracenyl groups, fluorenyl groups, and carbazolyl groupssubstituted with at least one substituent selected from C₁-C₅ alkylgroups, C₁-C₅ alkoxy groups, cyano groups, amine groups, phenoxy groups,phenyl groups and halogen groups. The substituted C₁₂-C₅₀ arylaminegroups may be selected from groups substituted with at least onesubstituent selected from C₁-C₅ alkyl groups, C₁-C₅ alkoxy groups, cyanogroups, amine groups, phenoxy groups, phenyl groups and halogen groups.

Each of R₂ and R₃ may be independently selected from methyl groups andphenyl groups.

Each of R₅ and R₁₀ may be independently selected from t-butyl groups,phenyl groups, naphthyl groups, and fluorenyl groups.

Hereinafter, substituents described with reference to Formula 1 will nowbe described in detail.

The unsubstituted C₁-C₅₀ alkyl group may be linear or branched.Nonlimiting examples of the alkyl group include methyl groups, ethylgroups, propyl groups, isobutyl groups, sec-butyl groups, pentyl groups,iso-amyl groups, hexyl groups, heptyl groups, octyl groups, nonanylgroups, and dodecyl groups. At least one hydrogen atom of the alkylgroup may be substituted with a substituent selected from heavy hydrogenatoms, halogen atoms, hydroxyl groups, nitro groups, cyano groups, aminogroups, amidino groups, hydrazines, hydrazones, carboxyl groups andsalts thereof, sulfonic acid groups and salts thereof, phosphoric acidgroups and salts thereof, C₁-C₁₀ alkyl groups, C₁-C₁₀ alkoxy groups,C₂-C₁₀ alkenyl groups, C₂-C₁₀ alkynyl groups, C₆-C₁₆ aryl groups, andC₄-C₁₆ heteroaryl groups.

The unsubstituted C₃-C₅₀ cycloalkyl group refers to a C₃-C₅₀ cycloalkylgroup. At least one hydrogen atom in the cycloalkyl group may besubstituted with a substituent such as those described above withrespect to the unsubstituted C₁-C₅₀ alkyl group.

The unsubstituted C₁-C₅₀ alkoxy group is a group having a structure of—OA wherein A is an unsubstituted C₁-C₅₀ alkyl group as described above.Nonlimiting examples of the alkoxy group include methoxy groups, ethoxygroups, propoxy groups, isopropyloxy groups, butoxy groups, and pentoxygroups. At least one hydrogen atom of the alkoxy group may besubstituted with a substituent such as those described above withrespect to the unsubstituted C₁-C₅₀ alkyl group.

The unsubstituted C₆-C₆₀ aryl group refers to a C₆-C₆₀ carbocyclicaromatic system containing at least one ring. When the C₆-C₆₀carbocyclic aromatic system contains at least two rings, they may befused to each other or linked to each other by a single bond. The term‘aryl’ refers to an aromatic system, such as phenyl, naphthyl, oranthracenyl. In the aryl, one or more hydrogen atoms may be substitutedwith a substituent such as those described above with respect to theunsubstituted C₁-C₅₀ alkyl group.

Nonlimiting examples of the substituted or unsubstituted C₆-C₃₀ arylgroup include phenyl groups, C₁-C₁₀ alkylphenyl groups (for example,ethylphenyl groups), halophenyl groups (for example, o-, m-, andp-fluorophenyl groups, dichlorophenyl groups), cyanophenyl groups,dicyanophenyl groups, trifluoromethoxyphenyl groups, biphenyl groups,halobiphenyl groups, cyanobiphenyl groups, C₁-C₁₀ alkyl biphenyl groups,C₁-C₁₀ alkoxybiphenyl groups, o-, m-, and p-tolyl groups, o-, m-, andp-cumenyl groups, mesityl groups, phenoxyphenyl groups,(α,α-dimethylbenzene)phenyl groups, (N,N′-dimethyl)aminophenyl groups,(N,N′-diphenyl)aminophenyl groups, pentalenyl groups, indenyl groups,naphthyl groups, halonaphthyl groups (for example, fluoronaphthylgroups), C₁-C₁₀ alkylnaphthyl groups (for example, methylnaphthylgroups), C₁-C₁₀ alkoxynaphthyl groups (for example, methoxynaphthylgroups), cyanonaphthyl groups, anthracenyl groups, azulenyl groups,heptalenyl groups, acenaphthylenyl groups, phenalenyl groups, fluorenylgroups, anthraquinolyl groups, methylanthryl groups, phenanthryl groups,triphenylene groups, pyrenyl groups, chrysenyl groups, ethyl-chrysenylgroups, picenyl groups, perylenyl groups, chloroperylenyl groups,pentaphenyl groups, pentacenyl groups, tetraphenylenyl groups,hexaphenyl groups, hexacenyl groups, rubicenyl groups, coronenyl groups,trinaphthylenyl groups, heptaphenyl groups, heptacenyl groups,pyranthrenyl groups, and ovalenyl groups.

The unsubstituted C₄-C₆₀ heteroaryl group includes one, two or threehetero atoms selected from N, O, P and S. When the C₄-C₆₀ heteroarylgroup contains at least two rings, they may be fused to each other orlinked to each other by a single bond. Nonlimiting examples of theunsubstituted C₄-C₆₀ heteroaryl group include pyrazolyl groups,imidazolyl groups, oxazolyl groups, thiazolyl groups, triazolyl groups,tetrazolyl groups, oxadiazolyl groups, pyridinyl groups, pyridazinylgroups, pyrimidinyl groups, triazinyl groups, carbazolyl groups, indolylgroups, quinolinyl groups, and isoquinolinyl groups. In the heteroarylgroup, one or more hydrogen atoms may be substituted with a substituentsuch as those described above with respect to the unsubstituted C₁-C₅₀alkyl group.

The unsubstituted C₅-C₅₀ aryloxy group is represented by —OA₁ where A₁may be a C₅-C₆₀ aryl group. Nonlimiting examples of the aryloxy groupinclude phenoxy groups. In the aryloxy group, one or more hydrogen atommay be substituted with a substituent such as those described above withrespect to the unsubstituted C₁-C₅₀ alkyl group.

The unsubstituted C₅-C₅₀ arylthio group is represented by —SA₁ where A₁may be a C₅-C₆₀ aryl group. Nonlimiting examples of the arylthio groupinclude phenylthio groups, naphthylthio groups, and fluorenylthiogroups. In the arylthio group, one or more hydrogen atoms may besubstituted with a substituent such as those described above withrespect to the unsubstituted C₁-C₅₀ alkyl group.

The unsubstituted C₆-C₆₀ condensed polycyclic group refers to asubstituent including at least two rings wherein at least one aromaticring and/or at least one non-aromatic ring are fused to each other. Theunsubstituted C₆-C₆₀ condensed polycyclic group may be substituted withat least one substituent such as those described above with respect tothe aryl group or the heteroaryl group.

Nonlimiting examples of the heterocyclic compound of Formula 1 accordingto embodiments of the present invention include Compounds 1 through 95represented below.

An organic light-emitting device according to an embodiment of thepresent invention includes a first electrode, a second electrode, and anorganic layer between the first electrode and the second electrode,wherein the organic layer includes the heterocylic compound of Formula 1described above.

The organic layer including the heterocyclic compound of Formula 1 maybe an electron injection layer (EIL), an electron transport layer (ETL),or a single layer having both electron injection and electron transportcapabilities. Alternatively, the organic layer including theheterocyclic compound of Formula 1 may be an EML. When the organic layerincluding the heterocyclic compound of Formula 1 is an EML, theheterocyclic compound of Formula 1 may be used as a fluorescent host, aphosphorescent host, or a fluorescent dopant.

In the organic light-emitting device according to embodiments of thepresent invention, when the EML, the EIL or the ETL includes theheterocyclic compound of Formula 1, the EML may include an anthracenecompound, an arylamine compound or a styryl compound. The anthracenecompound, the arylamine compound or the styryl compound may beunsubstituted or substituted with a substituent such as those describedabove with respect to the unsubstituted C₁-C₅₀ alkyl group.

In the organic light-emitting device according to embodiments of thepresent invention, when the EIL, ETL or EML includes the heterocycliccompound of Formula 1, a red EML, a green EML, a blue EML or a white EMLmay include a phosphorescent compound.

The first electrode may be an anode, and the second electrode may be acathode, but the reverse is also possible.

In the organic light-emitting device described above, the organic layermay further include at least one layer selected from a HIL, a HTL, anelectron blocking layer (EBL), an EML, a hole blocking layer (HBL), anETL and an EIL, if desired. For example, the organic light-emittingdevice according to embodiments of the present invention may have afirst electrode/HIL/EML/second electrode structure, a firstelectrode/HIL/HTL/EML/ETL/second electrode structure, or a firstelectrode/HIL/HTL/EML/ETL/EIL/second electrode structure. Alternatively,the organic light-emitting device may have a first electrode/singlelayer having both hole injection and hole transportcapabilities/EML/ETL/second electrode structure, or a firstelectrode/single layer having both hole injection and hole transportcapabilities/EML/ETL/EIL/second electrode structure.

The organic light emitting device according to embodiments of thepresent invention may be a top-emission type organic light-emittingdevice or a bottom-emission type organic light-emitting device.

Hereinafter, a method of manufacturing an organic light-emitting deviceaccording to an embodiment of the present invention will be describedwith reference to FIG. 1. FIG. 1 illustrates the structure of an organiclight-emitting device according to an embodiment of the presentinvention. Referring to FIG. 1, the organic light-emitting deviceincludes a substrate, a first electrode (anode), a HIL, a HTL, an EML,an ETL, an EIL, and a second electrode (cathode).

First, a first electrode is formed on a substrate by deposition orsputtering. The first electrode may be formed of a first electrodematerial having a high work function. The first electrode may be ananode or a cathode. The substrate may be any substrate commonly used inorganic light-emitting devices, and may be, for example, a glasssubstrate or a transparent plastic substrate having good mechanicalstrength, thermal stability, transparency, surface planarity, handlingconvenience, and water resistance. The first electrode material mayinclude at least one material selected from indium tin oxide (ITO),indium zinc oxide (IZO), tin oxide (SnO₂), zinc oxide (ZnO), aluminum(Al), silver (Ag), and magnesium (Mg), which have good conductivity, andmay form a transparent or reflective electrode.

Next, a HIL may be formed on the first electrode by various methods, forexample, vacuum deposition, spin coating, casting, Langmuir-Blodgett(LB) method, or the like. When the HIL is formed using vacuumdeposition, the deposition conditions may vary according to the compoundused to form the HIL, and the desired structural and thermalcharacteristics of the HIL to be formed. For example, the depositionconditions may include a deposition temperature of about 100 to about500° C., a vacuum pressure of about 10⁻⁸ to about 10⁻³ torr, and adeposition rate of about 0.01 to about 100 Å/sec.

When the HIL is formed using spin coating, the coating conditions mayvary according to the compound used to form the HIL, and the structuraland thermal properties of the HIL to be formed. For example, the coatingconditions may include a coating speed of about 2000 rpm to about 5000rpm, and a thermal treatment temperature of about 80° C. to about 200°C., wherein the thermal treatment removes the solvent after the coating.

The HIL material may include the heterocyclic compound of Formula 1described above. Alternatively, known HIL materials may also be used.Nonlimiting examples of HIL materials include phthalocyanine compoundssuch as copper phthalocyanine,4,4′,4″-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA),N,N′-di(1-naphthyl)-N,N′-diphenylbenzidine) (NPB), TDATA, 2-TNATA,polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS),polyaniline/camphor sulfonicacid (Pani/CSA), and(polyaniline)/poly(4-styrenesulfonate) (PANI/PSS).

The HIL may have a thickness of about 100 Å to about 10000 Å. In someembodiments, for example, the HIL has a thickness of about 100 Å toabout 1000 Å. When the HIL has a thickness within these ranges, the HILhas good hole injection characteristics without increasing drivingvoltage.

Then, a HTL may be formed on the HIL by vacuum deposition, spin coating,casting, LB method, or the like. When the HTL is formed using vacuumdeposition or spin coating, the deposition or coating conditions may besimilar to those used to form the HIL, although the deposition orcoating conditions may vary according to the material that is used toform the HTL.

The HTL material may include the heterocyclic compound of Formula 1described above. Alternatively, known HTL materials may be used.Nonlimiting examples of HTL materials include carbazole derivatives suchas N-phenylcarbazole and polyvinylcarbazole, and amine derivativeshaving an aromatic condensed ring, such as NPB, orN,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1-biphenyl]-4,4′-diamine(TPD). Among these materials, TCTA not only transports holes but alsoinhibits excitons from being diffused from the EML.

The HTL may have a thickness of about 50 Å to about 1000 Å. In someembodiments, for example, the HTL has a thickness of 100 Å to about 600Å. When the HTL has a thickness within these ranges, the HTL has goodhole transport characteristics without substantially increasing drivingvoltage.

Then, an EML may be formed on the HTL by vacuum deposition, spincoating, casting, LB method, or the like. When the EML is formed usingvacuum deposition or spin coating, the deposition or coating conditionsmay be similar to those used to form the HIL, although the depositionand coating conditions may vary according to the material that is usedto form the EML.

The EML may include the heterocyclic compound of Formula 1 describedabove. In particular, the heterocyclic compound of Formula 1 may be usedas a host or a dopant. The EML may include a variety of knownlight-emitting materials, in addition to the heterocyclic compound ofFormula 1. Alternatively, the EML may also include a known host anddopant. The dopant used to form the EML may include either a fluorescentdopant or a phosphorescent dopant.

Nonlimiting examples of the host include Alq₃,4,4′-N,N′-dicarbazole-biphenyl (CPB),9,10-di(naphthalene-2-yl)anthracene (ADN), and distyrylarylene (DSA).

Nonlimiting examples of red dopants include platinum(II)octaethylporphyrin (PtOEP), Ir(piq)₃, Btp₂Ir(acac), and DCJTB.

Nonlimiting examples of green dopants include Ir(ppy)₃, where “ppy”denotes phenylpyridine, Ir(ppy)₂(acac), Ir(mpyp)₃, and C545T.

Nonlimiting examples of blue dopants include F₂Irpic, (F₂ ppy)₂Ir(tmd),Ir(dfppz)₃, ter-fluorene, 4,4′-bis(4-diphenylaminostyryl)biphenyl(DPAVBi), and 2,5,8,11-tetra-t-butyl pherylene (TBPe).

The amount of the dopant may be about 0.1 to about 20 parts by weightbased on 100 parts by weight of the EML material (i.e., the total weightof the host and the dopant). In some embodiments, the amount of thedopant may be about 0.5 to about 12 parts by weight based on 100 partsby weight of the EML material. When the content of the dopant is withinthese ranges, concentration quenching may be substantially prevented.

The EML may have a thickness of about 100 Å to about 1000 Å. In someembodiments, for example, the EML has a thickness of about 200 Å toabout 600 Å. When the EML has a thickness within these ranges, the EMLhas good light-emitting characteristics without substantially increasingdriving voltage.

When the EML includes a phosphorescent dopant, a HBL (not shown inFIG. 1) may be formed on the EML to prevent diffusion of tripletexcitons or holes into the ETL. The HBL may be formed of any materialcommonly used to form a HBL, without limitation. Nonlimiting examples ofHBL materials include oxadiazole derivatives, triazole derivatives,phenanthroline derivatives, Balq, and BCP.

The HBL may have a thickness of about 50 Å to about 1000 Å. In someembodiments, for example, the HBL has a thickness of about 100 Å toabout 300 Å. When the thickness of the HBL is within these ranges, theHBL may have good hole blocking capability without substantiallyincreasing driving voltage.

Then, an ETL may be formed on the HBL or EML by vacuum deposition, spincoating, casting, or the like. When the ETL is formed using vacuumdeposition or spin coating, the deposition or coating conditions may besimilar to those used to form the HIL, although the deposition andcoating conditions may vary according to the material that is used toform the ETL.

The ETL material may include the heterocyclic compound of Formula 1described above. Alternatively, the ETL may be formed of any materialknown in the art. Nonlimiting examples of ETL materials includequinoline derivatives, such as tris(8-quinolinolate)aluminum (Alq₃),TAZ, or Balq.

The ETL may have a thickness of about 100 Å to about 1000 Å. In someembodiments, for example, the ETL has a thickness of about 100 Å toabout 500 Å. When the ETL has a thickness within these ranges, the ETLmay have good electron transport characteristics without substantiallyincreasing driving voltage.

In addition, an EIL, which facilitates injection of electrons from thecathode, may be formed on the ETL.

The EIL material may include the heterocyclic compound of Formula 1described above. Alternatively, known EIL materials, such as LiF, NaCl,CsF, Li₂O, or BaO, may be used to form the EIL. The deposition orcoating conditions may be similar to those used to form the HIL,although the deposition and coating conditions may vary according to thematerial that is used to form the EIL.

The EIL may have a thickness of about 1 Å to 100 Å. In some embodiments,for example, the EIL has a thickness of about 5 Å to about 90 Å. Whenthe EIL has a thickness within these ranges, the EIL may have goodelectron injection characteristics without substantially increasingdriving voltage.

Finally, a second electrode may be formed on the EIL by, for example,vacuum deposition, sputtering, or the like. The second electrode may bea cathode or an anode. The material for forming the second electrode maybe a metal, an alloy, or an electrically conductive compound with a lowwork function. Nonlimiting examples of second electrode materialsinclude lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium(Al—Li), calcium (Ca), magnesium-indium(Mg—In), and magnesium-silver(Mg—Ag). In addition, in order to manufacture a top-emission typeorganic light-emitting device, a transparent cathode formed of atransparent material such as ITO or IZO may be used.

The organic light-emitting device according to embodiments of thepresent invention may be included in various types of flat panel displaydevices, such as passive matrix organic light-emitting display devicesor active matrix organic light-emitting display devices. When theorganic light-emitting device is included in an active matrix organiclight-emitting display device including a thin-film transistor, thefirst electrode formed on the substrate may function as a pixelelectrode, and is electrically connected to a source electrode or adrain electrode of the thin-film transistor. Moreover, the organiclight-emitting device may also be included in flat panel display deviceshaving double-sided screens.

According to embodiments of the present invention, at least one layer ofthe organic light-emitting device may be formed of the heterocycliccompound of Formula 1 and may be applied by a deposition method or a wetmethod of coating a solution of the heterocylic compound of Formula 1.

The following examples are presented for illustrative purposes only, ando not limit the scope of the present invention.

EXAMPLES Synthesis Example Synthesis of Compound 11

Synthesis of Intermediate 1

27.3 g (100.0 mmol) of 2-bromo-9,9-dimethylfluorene, 11.2 g (120.0 mmol)of aniline, 14.4 g (150.0 mmol) of NaOt-Bu, 4.5 g (5.0 mmol) ofPd₂(dba)₃, and 1.0 g (5.0 mmol) of Pt-Bu₃ were dissolved in 300 ml oftoluene, and the mixture was maintained at 90° C. for 5 hours in anitrogen atmosphere. The mixture was cooled to room temperature, and 100mL of water was added thereto. Then, the mixture was subjected toextraction twice with 300 ml of methylene chloride. An organic layer wascollected and dried, followed by filtration and concentration. Theresidue was separated by column chromatography to obtain 20.1 g (yield:78%) of pale yellow Intermediate 1.

Synthesis of Intermediate 2

14.3 g (50.0 mmol) of Intermediate 1, 28.3 g (100.0 mmol) of4-bromoiodobenzene, 7.2 g (75.0 mmol) of NaOt-Bu, 2.3 g (2.5 mmol) ofPd₂(dba)₃, and 0.5 g (2.5 mmol) of Pt-Bu₃ were dissolved in 150 mL oftoluene, and the mixture was maintained at 90° C. for 5 hours in anitrogen atmosphere. The mixture was cooled to room temperature, and 50mL of water was added thereto. Then, the mixture was subjected toextraction twice with 200 ml of methylene chloride. An organic layer wascollected and dried, followed by filtration and concentration. Theresidue was separated by column chromatography to obtain 13.6 g (yield:62%) of pale yellow Intermediate 2. The structure of this compound wasidentified using high-resolution mass spectra (HR-MS). (calc.; 439.0936,found; 439.0923)

Synthesis of Intermediate 3

37.0 g (100.0 mmol) of 2-bromo-9,9′-di-t-butylanthracene, 20.3 g (120mmol) of benzophenone hydrazone, 14.4 g (150.0 mmol) of NaOt-Bu, 1.1 g(5.0 mmol) of Pd(Oac)₂, and 2.4 g (5.0 mmol) of 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl were dissolved in 300 mL oftoluene, and the mixture was maintained at 90° C. for 3 hours in anitrogen atmosphere. The mixture was cooled to room temperature, and 100mL of water was added thereto. Then, the mixture was subjected toextraction twice with 300 ml of methylene chloride. An organic layer wascollected and dried, followed by filtration and concentration. Theresidue was separated by column chromatography to obtain 39.7 g (yield:82%) of yellowish green solid Intermediate 3.

Synthesis of Intermediate 4

38.8 g (80.0 mmol) of Intermediate 3 and 30.4 g (160.0 mmol) ofp-toluene sulfonic acid were dissolved in 300 mL of methyl ethyl ketone,and the mixture was maintained at 80° C. for 12 hours in a nitrogenatmosphere. The mixture was cooled to room temperature, the solvent wasconcentrated under a reduced pressure, and 100 mL of water was addedthereto. Then, the mixture was subjected to extraction twice with 200 mlof methylene chloride. An organic layer was collected and dried,followed by filtration and concentration. The residue was separated bycolumn chromatography to obtain 16.9 g (yield: 58%) of yellowish brownsolid Intermediate 4.

Synthesis of Compound 11

10.7 g (30.0 mmol) of Intermediate 4, 15.5 g (36 mmol) of Intermediate2, 4.3 g (45.0 mmol) of NaOt-Bu, 1.4 g (1.5 mmol) of Pd₂(dba)₃, and 0.72g (1.5 mmol) of 2-dicyclohexyl phosphino-2′,4′,6′-triisopropylbiphenylwere dissolved in 100 mL of toluene, and the mixture was maintained at90° C. for 6 hours in a nitrogen atmosphere. The mixture was cooled toroom temperature, and 30 mL of water was added thereto. Then, themixture was subjected to extraction twice with 200 ml of methylenechloride. An organic layer was collected and dried, followed byfiltration and concentration. The residue was separated by columnchromatography to obtain 13.3 g (yield: 62%) of light green solidCompound 11. The structure of this compound was identified using HR-MS.(calc.; 716.4130, found; 716.4123), (1H-NMR, 400 MHz, CD2Cl2: δ7.88-6.89(m, 22H), δ2.43 (s, 3H), δ2.33 (s, 3H), δ1.73 (s, 6H), δ1.34 (s, 9H)13C-NMR: 141.3, 140.3, 139.2, 138.8, 136.9, 136.0, 135.7, 135.1, 133.4,133.1, 132.6, 131.2, 131.0, 130.6, 130.2, 129.6, 129.1, 128.6, 128.4,128.0, 127.6, 125.3, 125.5, 125.1, 124.8, 124.5, 124.3, 123.9, 123.3,121.9, 121.1, 120.6, 116.5, 115.4, 38.5, 34.4, 31.3, 30.2, 12.8, 11.5.)

Synthesis Example Synthesis of Compound 43

Synthesis of Intermediate 5

Intermediate 5 (44.6 g, yield: 82%) was prepared in the same manner asIntermediate 3, except that 40.9 g (100.0 mmol) of2-bromo-9,9′-diphenylanthracene was used.

Synthesis of Intermediate 6

41.9 g (80.0 mmol) of Intermediate 5, 30.4 g (160.0 mmol) of p-toluenesulfonic acid, and 40.2 g (160 mmol) of benzylphenylketone weredissolved in a mixed solution of 200 mL of toluene and 50 mL of ethanol,and the mixture was maintained at 100° C. for 12 hours in a nitrogenatmosphere. The mixture was cooled to room temperature, the solvent wasconcentrated under a reduced pressure, and 100 mL of water was addedthereto. Then, the mixture was subjected to extraction twice with 200 mlof methylene chloride. An organic layer was collected and dried,followed by filtration and concentration. The residue was separated bycolumn chromatography to obtain 25.0 g (yield: 60%) of yellowish brownsolid Intermediate 6.

Synthesis of Compound 43

Compound 43 (14.2 g, yield: 62%) was prepared in the same manner asCompound 11, except that 15.7 g (30.0 mmol) of Intermediate 6 and3-iodo-N-phenylcarbazole were used. The structure of this compound wasidentified using HR-MS. (calc.; 762.9357, found; 762.9344), (1H-NMR, 400MHz, CD2Cl2: δ8.10-7.84 (m, 2H), δ7.68-6.89 (m, 36H), 13C-NMR: 140.3,140.0, 139.1, 138.8, 137.9, 136.8, 135.7, 135.1, 134.4, 133.8, 132.6,131.0, 130.6, 130.0, 129.6, 129.0, 128.2, 128.0, 127.2, 127.0, 126.3,125.5, 125.1, 124.8, 124.5, 124.3, 123.9, 123.3, 121.9, 121.1, 120.6,120.1, 119.6, 118.5, 118.3, 116.5, 115.4)

Synthesis Example Synthesis of Compound 56

Synthesis of Intermediate 7

48.8 g (100.0 mmol) of 2,6-dibromo-9,9′-diphenylanthracene, 8.6 g (30.0mmol) of Intermediate 1, 4.3 g (45.0 mmol) of NaOt-Bu, 1.4 g (1.5 mmol)of Pd₂(dba)₃, and 0.30 g (1.5 mmol) of Pt-Bu₃ were dissolved in 200 mlof toluene, and the mixture was maintained at 90° C. for 3 hours in anitrogen atmosphere. The mixture was cooled to room temperature, and 100mL of water was added thereto. Then, the mixture was subjected toextraction twice with 300 ml of methylene chloride. An organic layer wascollected and dried, followed by filtration and concentration. Theresidual 2,6-dibromo-9,9′-diphenylanthracene (20.5 g, 42.0 mmol) wascollected by filtration, and the residue was separated by columnchromatography to obtain 9.4 g (yield: 45%) of light yellow solidIntermediate 7.

Synthesis of Intermediate 8

13.8 g (20.0 mmol) of Intermediate 7, 5.1 g (30 mmol) ofbenzophenonehydrazone, 2.9 g (30.0 mmol) of NaOt-Bu, 1.4 g (1.5 mmol) ofPd(OAc)₂, and 2.4 g (1.5 mmol) of 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl were dissolved in 80 mL oftoluene, and the mixture was maintained at 90° C. for 3 hours in anitrogen atmosphere. The mixture was cooled to room temperature, and 100mL of water was added thereto. Then, the mixture was subjected toextraction twice with 300 ml of methylene chloride. An organic layer wascollected and dried, followed by filtration and concentration. Theresidue was separated by column chromatography to obtain 13.7 g (yield:85%) of yellow solid Intermediate 8.

Synthesis of Intermediate 9

Intermediate 9 (6.2 g, yield: 51% was synthesized in the same manner asIntermediate 6, except that 12.1 g (0.015 mmol) of Intermediate 8 wasused.

Synthesis of Compound 56

Compound 56 (6.8 g, yield: 73%) was synthesized in the same manner asCompound 11, except that 8.1 g (10.0 mmol) of Intermediate 9 and 3.1 g(15.0 mmol) of 2-bromonaphthalene were used. The structure of thiscompound was identified using HR-MS. (calc.; 930.3974, found; 930.3979),(1H-NMR, 400 MHz, CD2Cl2: δ7.98-6.69 (m, 44H), 13C-NMR: 140.1, 140.0,139.1, 138.9, 138.5, 137.4, 137.1, 136.3, 135.2, 135.1, 134.7, 134.4,133.8, 133.4, 132.9, 132.6, 131.8, 131.0, 130.6, 130.0, 129.6, 129.0,128.6, 128.4, 128.2, 128.0, 127.2, 127.0, 126.3, 125.5, 125.1, 124.8,124.5, 124.3, 123.9, 123.3, 122.8, 122.2, 121.9, 121.1, 120.6, 120.1,119.6, 118.5, 118.3, 116.5, 115.4)

Synthesis Example Synthesis of Compound 74

Synthesis of Intermediate 10

Intermediate 10 (46.9 g, yield: 75%) was synthesized in the same manneras Intermediate 3, except that 51.0 g (100.0 mmol) of2-bromo-9,9′-di-2-naphthylanthracene was used.

Synthesis of Intermediate 11

Intermediate 11(16.5 g, yield: 54%) was synthesized in the same manneras Intermediate 6, except that 31.2 g (50.0 mmol) of Intermediate 10 wasused.

Synthesis of Compound 74

Compound 74 (9.0 g, yield: 60%) was synthesized in the same manner asCompound 11, except that 12.4 g (20.0 mmol) of Intermediate 11 and 6.2 g(30.0 mmol) of 2-bromonaphthalene were used. The structure of thiscompound was identified using HR-MS. (calc.; 747.2926, found; 747.2915),(1H-NMR, 400 MHz, CD2Cl2: δ7.90-7.02 (m, 37H), 13C-NMR: 140.4, 140.2,139.7, 138.9, 138.3, 137.6, 137.5, 137.3, 135.2, 135.1, 134.7, 134.4,133.7, 133.3, 132.9, 132.3, 131.8, 131.5, 130.7, 130.0, 129.3, 129.0,128.6, 128.4, 128.2, 128.0, 127.6, 127.0, 126.3, 125.5, 125.1, 124.8,124.5, 124.3, 123.9, 122.8, 122.2, 121.9, 120.6, 119.6, 118.5, 118.3)

Synthesis Example Synthesis of Compound 82

Synthesis of Intermediate 12

Intermediate 12 (59.0 g, yield: 78%) was synthesized in the same manneras Intermediate 3, except that 64.1 g (100.0 mmol) of2-bromo-9,9′-di-9,9-dimethylfluorenylanthracene was used was used.

Synthesis of Intermediate 13

Intermediate 13 (26.5 g, yield: 60%) was synthesized in the same manneras Intermediate 4, except that 53.0 g (70.0 mmol) of Intermediate 12 wasused.

Synthesis of Compound 82

Compound 82 (9.9 g, yield: 66%) was synthesized in the same manner asCompound 74, except that 12.6 g (20.0 mmol) of Intermediate 13 was used.The structure of this compound was identified using HR-MS. (calc.;755.3552, found; 755.3545), (1H-NMR, 400 MHz, CD2Cl2: δ7.90-7.02 (m,37H), δ2.43 (s, 3H), δ2.32 (s, 3H), δ1.32 (s, 6H), δ1.28 (s, 6H),13C-NMR: 141.4, 141.2, 140.5, 140.0, 139.7, 138.6, 138.3, 137.6, 137.3,136.5, 136.1, 135.2, 135.1, 134.7, 134.4, 133.7, 133.3, 132.9, 132.3,131.8, 131.5, 130.7, 130.0, 129.3, 129.0, 128.6, 128.4, 128.2, 128.0,127.6, 127.0, 126.6, 125.5, 125.2, 124.8, 124.6, 124.4, 123.2, 122.2,120.6, 119.6, 118.5, 26.5, 26.3, 18.4, 18.2, 13.2, 13.1)

Synthesis Example Synthesis of Compound 29

Synthesis of Intermediate 14

27.3 g (100.0 mmol) of 2-bromo-9,9-dimethylfluorene was dissolved in 200mL of THF, the solution was cooled to −78° C., and 44 mL (2.5 M inhexane, 110 mmol) of butyl lithium was slowly dropwise added to thesolution in a nitrogen atmosphere. The reaction temperature wasmaintained at −78° C. for 30 minutes, raised to −30° C. and cooled againto −78° C. Then, 16.8 mL (150 mmol) of trimethylborate was slowlydropwise added to the reaction product, and the temperature was raisedto room temperature and maintained for 2 hours. 50 mL of 1 N HClsolution was slowly dropwise added to the reaction mixture andmaintained for 30 minutes. 100 mL of water was further added to thereaction mixture, and the reaction mixture was subjected to extractiontwice with 200 ml of ethylacetate. An organic layer was collected anddried, followed by filtration and concentration. The residue wasseparated by column chromatography to obtain 16.4 g (yield: 69%) ofwhite solid Intermediate 14.

Synthesis of Intermediate 15

11.9 g (50.0 mmol) of Intermediate 14, 28.3 g (100.0 mmol) ofbromoiodobenzene, 3.5 g (3.0 mmol) of Pd(PPh₃)₄, and 8.0 g (200 mmol) ofNaOH were dissolved in a mixed solution of 150 mL of THF and 50 mL ofwater, and the mixture was maintained at 70° C. for 12 hours. Themixture was cooled to room temperature, and 100 mL of water was addedthereto. Then, the mixture was subjected to extraction twice with 200 mlof methylene chloride. An organic layer was collected and dried,followed by filtration and concentration. The residue was separated bycolumn chromatography to obtain 11.4 g (yield: 64%) of white solidIntermediate 15.

Synthesis of Intermediate 16

44.8 g (100.0 mmol) of 2,6-dibromo-9,9′-di-t-butylanthracene, 3.4 g (20mmol) of 2-naphthylboronic acid, 1.2 g (1.0 mmol) of Pd(PPh₃)₄, and 3.2g (80 mmol) of NaOH were dissolved in a mixed solution of 150 mL of THFand 50 mL of water, and the mixture was maintained at 70° C. for 12hours. The mixture was cooled to room temperature, and 100 mL of waterwas added thereto. Then, the mixture was subjected to extraction twicewith 200 ml of methylene chloride. An organic layer was collected anddried, followed by filtration and concentration. The residual2,6-dibromo-9,9′-di-t-butylanthracene (22.4 g, 50.0 mmol) was separatedby column chromatography and recrystallization to obtain 6.1 g (yield:61%) of light yellow solid Intermediate 16.

Synthesis of Intermediate 17

Intermediate 17 (6.2 g, yield: 84%) was synthesized in the same manneras Intermediate 3, except that 5.9 g (12.0 mmol) of Intermediate 16 wasused.

Synthesis of Intermediate 18

Intermediate 18 (2.9 g, yield: 67%) was synthesized in the same manneras Intermediate 4, except that 5.5 g (9.0 mmol) of Intermediate 17 wasused.

Synthesis of Compound 29

Compound 29 (3.2 g, yield: 70%) was synthesized in the same manner asCompound 11, except that 2.9 g (6.0 mmol) of Intermediate 18 and 3.1 g(9.0 mmol) of Intermediate 15 were used. The structure of this compoundwas identified using HR-MS. (calc.; 751.4178, found; 71.4169), (1H-NMR,400 MHz, CD2Cl2: δ8.02-7.02 (m, 23H), δ2.43 (s, 3H), δ2.32 (s, 3H),δ1.62 (s, 6H), δ1.47 (s, 9H), δ1.45 (s, 9H) 13C-NMR: 140.5, 140.1,139.4, 138.6, 138.4, 137.6, 137.0, 136.7, 136.2, 135.2, 135.1, 134.8,134.4, 133.7, 133.3, 132.9, 132.3, 131.8, 131.5, 130.3, 130.0, 129.3,129.0, 128.6, 128.4, 128.2, 128.0, 127.6, 127.0, 126.8, 125.6, 125.2,124.9, 124.6, 124.4, 122.2, 120.6, 119.6, 118.5, 26.6, 26.3, 18.4, 18.2,13.2, 13.1)

Example 1

An anode was prepared by cutting a Corning 15 Ωcm²(1200 Å) ITO glasssubstrate to a size of 50 mm×50 mm×0.7 mm, ultrasonically cleaning theglass substrate using isopropyl alcohol and pure water for 5 minuteseach, and then irradiating with UV light for 30 minutes and exposing toozone to clean. Then, the anode was mounted in a vacuum depositionapparatus.

Then, 2-TNATAas an HIL material was vacuum-deposited on the glasssubstrate to form a HIL having a thickness of 600 Å. Then,4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) as a hole transportcompound was vacuum deposited on the HIL to form a HTL having athickness of 300 Å.

9,10-di-naphthalene-2-yl-anthracene (ADN) as a blue fluorescent host andCompound 11 as a blue fluorescent dopant were simultaneously depositedat a weight ratio of 98:2 on the HTL to form an EML having a thicknessof 300 Å.

Then, Alq₃ was deposited on the EML to form an ETL having a thickness of300 Å, and then LiF (a halogenated alkali metal) was deposited on theETL to form an EIL having a thickness of 10 Å. Then, Al was deposited onthe EIL to a thickness of 3000 Å (cathode), thereby forming a LiF/Alelectrode. As a result, the manufacture of an organic light-emittingdevice was completed.

Example 2

An organic light-emitting device was manufactured in the same manner asExample 1, except that Compound 29 was used instead of Compound 11 toform the EML.

Example 3

An organic light-emitting device was manufactured in the same manner asExample 1, except that Compound 43 was used instead of Compound 11 toform the EML.

Example 4

An organic light-emitting device was manufactured in the same manner asExample 1, except that Compound 56 was used instead of Compound 11 toform the EML.

Example 5

An organic light-emitting device was manufactured in the same manner asExample 1, except that Compound 74 was used instead of Compound 11 toform the EML.

Example 6

An organic light-emitting device was manufactured in the same manner asExample 1, except that Compound 82 was used instead of Compound 11 toform the EML.

Example 7

An organic light-emitting device was manufactured in the same manner asExample 1, except that Compound 82 was used instead of Alq₃ to form theETL.

Comparative Example 1

An organic light-emitting device was manufactured in the same manner asExample 1, except that 1,4-bis-(2,2-diphenylvinyl)biphenyl) (DPVBi) wasused as a blue fluorescent dopant instead of Compound 11 to form theEML.

The organic light-emitting devices manufactured using the heterocycliccompounds of Formula 1 according to embodiments of the present inventionhad driving voltages that were lower by 1 V or greater than the deviceusing DPVBi, and thus had higher efficiency and good I-V-Lcharacteristics. In particular, lifetime characteristics were markedlyimproved by 100% or greater in the organic light-emitting devicesaccording to Examples 1 through 7 as compared to the organiclight-emitting device according to Comparative Example 1. The resultsare shown in Table 1 below.

TABLE 1 Emitting material or light- electron emission transportingDriving Current efficiency Emitted Half-life span material voltagedensity Brightness (cd/A) color (hr @ 100 mA/cm²) Example 1 Compound 116.27 50 2,850 5.70 blue 238 hr Example 2 Compound 29 6.13 50 3,045 6.09blue 241 hr Example 3 Compound 43 6.30 50 2,910 5.82 blue 268 hr Example4 Compound 56 6.41 50 3,520 7.04 blue 275 hr green Example 5 Compound 746.33 50 3,372 6.74 blue 288 hr green Example 6 Compound 82 6.14 50 3,0706.14 blue 283 hr Example 7 Compound 82 5.75 50 3,470 6.94 blue 345 hrComparative DPVBi 7.85 50 1,560 3.12 blue 113 hr Example 1

The heterocyclic compounds according to embodiments of the presentinvention have good electrical characteristics, charge transportingcapabilities, and light-emitting characteristics, high glass transitiontemperatures (Tg), and crystallization prevention characteristics. Thus,the heterocyclic compounds may be used as electron transportingmaterials for all-color fluorescent and phosphorescent devices, such asred, green, blue, and white fluorescent and phosphorescent devices, oras an emitting material for green, blue, and white fluorescent andphosphorescent devices. Thus, organic light-emitting devices having highefficiency, low driving voltages, high brightness and long lifespans maybe manufactured using the heterocylic compounds.

While the present invention has been illustrated and described withreference to certain exemplary embodiments, it is understood by those ofordinary skill in the art that various modifications and changes may bemade to the described embodiments without departing from the spirit andscope of the present invention as defined by the following claims.

1. A heterocyclic compound comprising a compound represented by Formula1 below:

wherein each of R₁ through R₁₁ is independently selected from the groupconsisting of hydrogen atoms, heavy hydrogen atoms, substituted andunsubstituted C₁-C₅₀ alkyl groups, substituted and unsubstituted C₃-C₅₀cycloalkyl groups, substituted and unsubstituted C₁-C₅₀ alkoxy groups,substituted and unsubstituted C₅-C₅₀ aryloxy groups, substituted andunsubstituted C₅-C₅₀ arylthio groups, substituted and unsubstitutedC₅-C₆₀ aryl groups, amino groups substituted with at least one R₅-R₅₀aryl group, substituted and unsubstituted C₄-C₆₀ heteroaryl groups,substituted and unsubstituted C₆-C₆₀ condensed polycyclic groups,halogen atoms, cyano groups, nitro groups, hydroxyl groups, and carboxylgroups, wherein two or more neighboring substituents selected from R₁through R₁₁ may optionally combine to form an aromatic ring.
 2. Theheterocyclic compound of claim 1, wherein R₁ is selected from the groupconsisting of: unsubstituted monocyclic to tricyclic aryl groupsselected from the group consisting of phenyl groups, naphthyl groups,biphenyl groups, terphenyl groups, anthracenyl groups, fluorenyl groups,and carbazolyl groups; and substituted monocyclic to tricyclic arylgroup selected from the group consisting of phenyl groups, naphthylgroups, biphenyl groups, terphenyl groups, anthracenyl groups, fluorenylgroups, and carbazolyl groups substituted with at least one substituentselected from the group consisting of C₁-C₅ alkyl groups, C₁-C₅ alkoxygroups, cyano groups, amine groups, phenoxy groups, phenyl groups andhalogen groups.
 3. The heterocyclic compound of claim 1, wherein R₇ isselected from the group consisting of: unsubstituted monocyclic totricyclic aryl groups selected from the group consisting of phenylgroups, naphthyl groups, biphenyl groups, terphenyl groups, anthracenylgroups, fluorenyl groups and carbazolyl groups; unsubstituted C₁₂-C₅₀arylamine groups; substituted monocyclic to tricyclic aryl groupselected from the group consisting of phenyl groups, naphthyl groups,biphenyl groups, terphenyl groups, anthracenyl groups, fluorenyl groups,and carbazolyl groups substituted with at least one substituent selectedfrom the group consisting of C₁-C₅ alkyl groups, C₁-C₅ alkoxy groups,cyano groups, amine groups, phenoxy groups, phenyl groups, and halogengroups; and C₁₂-C₅₀ arylamine groups substituted with at least onesubstituent selected from the group consisting of C₁-C₅ alkyl groups,C₁-C₄ alkoxy groups, cyano groups, amine groups, phenoxy groups, phenylgroups, and halogen groups.
 4. The heterocyclic compound of claim 1,wherein each of R₂ and R₃ is independently selected from the groupconsisting of methyl groups and phenyl groups.
 5. The heterocycliccompound of claim 1, wherein each of R₅ and R₁₀ is independentlyselected from the group consisting of t-butyl groups, phenyl groups,naphthyl groups, and fluorenyl groups.
 6. The heterocyclic compound ofclaim 1, wherein the compound represented by Formula 1 comprises acompound selected from the group consisting of Compounds 11, 29, 43, 56,74 and 82:


7. An organic light-emitting device comprising: a first electrode; asecond electrode; and an organic layer between the first electrode andthe second electrode, wherein the organic layer comprises theheterocyclic compound of claim
 1. 8. The organic light-emitting deviceof claim 7, wherein the organic layer comprises an electron injectionlayer or an electron transport layer.
 9. The organic light-emittingdevice of claim 7, wherein the organic layer comprises a single layerhaving both electron injection and electron transport capabilities. 10.The organic light-emitting device of claim 7, wherein the organic layercomprises an emission layer.
 11. The organic light-emitting device ofclaim 7, wherein the organic layer comprises an emission layer, and theheterocylic compound is a host for the emission layer of a fluorescentor phosphorescent device.
 12. The organic light-emitting device of claim7, wherein the organic layer comprises an emission layer, and theheterocylic compound is a fluorescent dopant of the emission layer. 13.The organic light-emitting device of claim 7, wherein the organic layercomprises an emission layer, and an electron injection layer or anelectron transport layer, wherein the emission layer comprises ananthracene compound or an arylamine compound or a styryl compound. 14.The organic light-emitting device of claim 7, wherein the organic layercomprises an emission layer, and an electron injection layer or anelectron transport layer, wherein the emission layer comprises a redemission layer, a green emission layer, a blue emission layer or a whiteemission layer that comprises a phosphorescent compound.
 15. The organiclight-emitting device of claim 7, wherein the organic layer comprises atleast one layer selected from the group consisting of a hole injectionlayer, a hole transport layer, an electron blocking layer, an emissionlayer, a hole blocking layer, an electron transport layer, and anelectron injection layer.
 16. The organic light-emitting device of claim15, wherein the organic light-emitting device comprises a firstelectrode/hole injection layer/emission layer/second electrodestructure, or a first electrode/hole injection layer/hole transportlayer/emission layer/electron transport layer/second electrodestructure, or a first electrode/hole injection layer/hole transportlayer/emission layer/electron transport layer/electron injectionlayer/second electrode layer structure.
 17. A flat panel display device,comprising the organic light-emitting device of claim 7, wherein thefirst electrode of the organic light-emitting device is electricallyconnected to a source electrode or a drain electrode of a thin-filmtransistor.
 18. An organic light-emitting device comprising: a firstelectrode; a second electrode; and an organic layer between the firstelectrode and the second electrode, wherein the organic layer comprisesat least one layer comprising the heterocyclic compound of claim 1, theat least one layer being formed using a wet process.